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The Fashion Industry’s 10 Most Controversial Couples Ever

The Fashion Industry’s 10 Most Controversial Couples Ever

14,738 May 29th, 2013
Posted in Fashion By
  • "The Great Gatsby" World Premiere - Inside Arrivals

    Jenna Lyons and Courtney Crangi: When you think of Jenna Lyons, you probably think print-mixing, a colored heel, and her trademark glasses—but also her relationship with jewelry designer girlfriend Courtney Crangi, who she began seeing following her split from artist husband Vincent Mazeau. There has been plenty of speculation that Crangi broke up the marriage, and Mazeau reportedly hates how serious they have gotten—appearing in photoshoots, on red carpets, and all around the New York fashion scene. Regardless, it seems like the couple is happy—and no one can question their fabulous fashion sense.

    Photo: Getty Images / Stephen Lovekin
  • Christian Louboutin Cocktail Party

    Calvin Klein and Nick Gruber: Where do we begin? With the stats, perhaps: Klein is 70, worth $700 million, and is one of the most successful fashion designers of all time. Meanwhile, Gruber is 23, a former porn star, a rehab alum, and a convicted criminal (assault charges and cocaine, natch). Nonetheless, after over a year apart, the duo is reportedly hot and heavy again after a Memorial Day trip to Mexico.

    Photo: Getty Images / Cindy Ord
  • Exclusive... Mary-Kate Olsen & Olivier Sarkozy Fly Out Of Paris - No Internet Use Without Prior Agreement

    Mary-Kate Olsen and Olivier Sarkozy: As one half of the design team behind The Row and Elizabeth and James, Olsen is one of fashion's youngest and brightest power players. The 26-year-old mogul began dating 43-year-old ladies man and French financier (and brother of former French president Nicolas) Olivier Sarkozy last year, and they've been forced to withstand media scrutiny ever since. People scoff at the age difference, and also the fact that he's not shy when it comes to dramatic public displays of affection at basketball games—where they're frequently spotted courtside.

    Photo: Stylecaster Pictures / CHP/FAMEFLYNET
  • STEPHANIE.jpg

    Stephanie Seymour and John Casablancas: Long before she was the mother of gadabouts Peter and Harry Brant, Seymour was a 16-year-old who started a scandalous relationship with the married 41-year-old head of Elite Model Management, John Casablancas. The duo were a hit on the New York social scene, and they quickly began living together before she broke off the relationship. Their dramatic and controversial courtship was just the beginning of Seymour's storied romantic life. She later dated rocker Axl Rose and starred in his music video for "November Rain," prior to filing abuse charges against him. 

    Photo: Stylecaster Pictures /
  • 3rd Annual amfAR Inspiration Gala New York - Runway

    Marc Jacobs and Harry Louis: Calvin Klein isn't the only famous designer to dip his toes in the porn star pond—in fact, Marc Jacobs was doing it way before Klein was out of the closet. His latest 24-year-old squeeze is Harry Louis, a Brazilian porn star who has his own line of chocolates. Unlike Klein and Nick Gruber, they seem slightly more well-matched. Perhaps it's because Jacobs is 50—which is only twice Louis' age. Regardless, these gentlemen do making a dashing couple—and their bathing suit photos on a Brazilian beach recently caused an Internet sensation.

    Photo: Getty Images / Dimitrios Kambouris
  • Dan Peres And Kevin Martinez Host A DETAILS Magazine Cocktail Party To Celebrate Milan Men's Fashion Week

    Stefano Gabbana and Domenico Dolce: The men behind Dolce & Gabbana shot to fame after founding their eponymous label back in 1985, and were also a couple for years. Although they eventually called it quits back in 2005, their working relationship hasn't ceased—but sadly for them, it hasn't been all sunshine and couture. After being fined $440 million last month for tax evasion, the prosecutor is now stating that they should both be put behind bars. Eek!

    Photo: Getty Images / Harold Cunningham
  • amfAR New York Gala To Kick Off Fall 2011 Fashion Week - Inside

    Anna Wintour and Shelby Bryan: These days, legendary Vogue editrix Wintour and her entrepreneur beau Bryan are two of New York's most influential power players. But back in 1998, they were the victims of tabloid fodder following an affair that led them both to divorce their respective spouses. These days, despite their social prominence, Bryan still can't totally escape negative press—in January, it was reported that he owed over $1.2 million in back taxes.

    Photo: Getty Images / Larry Busacca
  • KATEMOSS.jpg

    Kate Moss and Pete Doherty: Well, here's one for the record books. 39-year-old British model and known party girl first began dating the 33-year-old known heroin addict after meeting at her birthday party in 2005. Two years later, he announced that they were engaged. Months later, they had split. Then they were back on, then off again. They became a tabloid sensation in the UK thanks to her substance-fueled antics, and their party pals included troubled stars like Amy Winehouse. It seems like Moss is way better off these days, married to rocker beau Jamie Hince, but it's not clear as to what's going on with Doherty.

    Photo: Stylecaster Pictures /
  • "PUNK: Chaos To Couture" Costume Institute Gala

    Kim Kardashian and Kanye West: Yes, we kno their primary occupations are sex-tape star-turned reality TV mogul and rapper, but let's face it: These days, KimYe are a fashion power couple—and a controversial one at that. It was a big deal when a pregnant Kardashian strutted down the Met Gala red carpet this year, especially since last year she'd been reportedly banned by Anna Wintour herself. Both of their everyday fashion choices have caused controversy as well—people have responded negatively to her maternity fashion choices, and let's not get started on his kilts and poorly reviewed fashion line.

    Photo: Getty Images / Larry Busacca
  • 14th Annual Warner Bros. And InStyle Golden Globe Awards After Party - Arrivals

    Miranda Kerr and Orlando Bloom: Although they are one of our favorite couples, the gorgeous actor and model duo are always in the tabloids for breakup rumors. While many would guess that it would be 36-year-old Bloom who steps out on his 30-year-old Victoria's Secret Angel wife, sources allege that Kerr has been involved with Leonardo DiCaprio as well as Gerard Butler. Just last week, fans exploded on Instagram after she posted a photo of herself and a male fashion photographer. Fingers crossed that these two will be together for the long haul so they can make more beautiful babies, but they've certainly seen a lot of controversy.

    Photo: Getty Images / Jason Merritt

We imagine it’s particularly difficult to be yourself when you’re constantly in the public eye. Not only are your sartorial and beauty choices scrutinized every time you leave your house or appear at a high-profile event, but your romantic life is immediately put on display and judged by everyone who witnesses your choices. And this doesn’t just apply to Hollywood starlets and B-list reality TV favorites—the fashion community has had its fair share of controversial couples who have been slammed in the gossip columns.

From industry power players like Jenna Lyons and girlfriend Courtney Crangi to Vogue editrix Anna Wintour and her entrepreneur beau Shelby Bryan, there’s been tons of tabloid fodder surrounding folks who you usually think about simply for their street style merits and enviable careers.

In honor of incessant gossip regarding Calvin Klein getting back together with his 23-year-old boy toy Nick Gruber, we decided to take a look at the industry’s 10 most controversial couples of all time.

Click through the slideshow above and let us know who you think is the most scandalous!

More on StyleCaster:
The 10 Most Controversial Celebrity Outfits Ever
The 6 Most Controversial Couples Attending the Met Gala
Report: Calvin Klein and His 23-Year-Old Boy Toy Have Reconciled

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